As a youngster growing up in Norfolk, Sarah DiPeppe loved collecting souvenir pennants from trips to Luray Caverns and Cape Hatteras in the Outer Banks.
More recently, DiPeppe has made it her mission to help Richmonders commemorate their love of the River City in the same way. In 2021, she officially launched Freak Flags, a creative endeavor that sells Richmond-specific felt pennants with slogans like “Strawberry Street Forever,” “Richmond River Rats” and “My Side Piece’s Name is James.”
Freak Flags was born in the uncertain days of the early pandemic.
“I worked at VDOT at the time, and we were all sent home,” explains DiPeppe, a local digital content manager. “It’s my COVID baby.”
The first Freak Flag was a literal one, simply reading “Freak” and “RVA.” Other early efforts included “Home, Home on the James,” “Sexy Cat Ladies of Richmond” and a Monument Avenue pennant that states “All Confederates are Bastards.” The latter two are still bestsellers, as is DiPeppe’s more recent “Witchmond” flag. Pennants for The Fan and the Museum District are also perennial favorites.
“I love Richmond and fell in love with it over the past 14, 15 years that I’ve lived here,” DiPeppe says. “[Freak Flags is] my gift to Richmond and a little love letter to the pieces of the city that I love.”
DiPeppe aims for a vintage look in her designs, which are created in collaboration with Buffalo, New York-based manufacturer Oxford Pennant.
“They’re like the king of the pennant castle in this country,” DiPeppe explains.
Freak Flags has issued roughly 50 different pennants over the years, with some popular flags reissued in different colorways. Thirty is the average run for a pennant.
“They’re really small batch,” DiPeppe says. “I don’t produce a lot. I want them to be fresh and new and make room for new styles as much as I can.”
One popular newer design reads “I Heart Train Noise,” a riff on the “I Heart Jet Noise” bumper stickers seen in Hampton Roads. Following the release of Cardi B and Megan Thee Stallion’s “WAP,” DiPeppe’s “Certified Freak” pennant sold well, a riff on the lyric “certified freak, seven days a week.”
Every fall, DiPeppe issues a run of her “Black Line,” comprised of the following pennants with black backgrounds: “Witchmond,” Hollywood Cemetery, Monument Avenue and “Keep Richmond Freaky.” For the past two years, she’s sold the Black Line at the Halloween Market at Helen’s.
Any duds? DiPeppe says that as much as people begged her to do a Northside and Manchester pennants, they didn’t sell well.
Though pennants date back centuries, the novelty felt pennant as we know it today was created in 1898 to promote school spirit and camaraderie at Ivy League schools. Their popularity exploded when American sports teams embraced the pennant, sometimes commemorating historic games or celebrating specific players. The industry was curtailed in the 1950s and ’60s with the emergence of sports merchandise licensing, but home décor trends have embraced the novelty felt pennant in recent years.
DiPeppe stresses the mobility and affordability of the felt pennant.
“Pennants are easy to hang up,” she says. “They’re easy to move. They’re easy to gift. It’s cheap to ship and hang.”
As Freak Flags is a side hustle, the pennants aren’t always for sale. Instead, DiPeppe does drops online and appears at pop-up markets throughout the year. Though Freak Flags decorate the interiors of Garnett’s, Rest in Pieces, Grisette and Jardin, only one brick and mortar location currently sells DiPeppe’s pennants: the Maymont gift shop carries a handful of Maymont pennants. DiPeppe says she’d love to sell Freak Flags at shops around the city in the future.
In the next few months DiPeppe hopes to offer flags celebrating Oregon Hill, Bamboo Café, iconic cats of Richmond, sandwiches, and one honoring The Diamond. In the next year, the Richmond Flying Squirrels will be begin playing at the new CarMax Park stadium; The Diamond will be demolished as part of the Diamond District redevelopment plan at an unspecified date.
“I’m a huge, huge Squirrels fan, and the last season at the Diamond is hitting very hard, so I’m doing an ode to The Diamond,” she explains.
More than just simple decorations, pennants can take on personal meaning, DiPeppe says. Some Richmonders who move away fight their homesickness with her “Carry Me Back to Richmond” pennant. One woman honors her late mother with a “Strawberry Street Forever” pennant as they used to enjoy bathtub brunches at Strawberry Street Café together.
Freak Flags currently has a fresh batch of banners for sale online, and DiPeppe will conduct in-person sales on Aug. 9 at Sneed’s Nursery for Cricket Day, a cat-themed market that celebrates the garden center’s resident cat Cricket.
DiPeppe admits that those who approach her should be ready for a conversation.
“I’m a yapper,” she says. “Be ready to talk if you’re going to come up.”
